Issue 17, 2023

Biocatalytic asymmetric reduction of fluoroalkyl ketones to access enantiopure fluoroalkyl secondary alcohols

Abstract

An efficient biocatalytic reduction of difluoroalkyl ketones for accessing chiral fluoroalkyl secondary alcohols is reported using commercial NADPH-dependent ketoreductase K234 with 2-propanol as a co-substrate for NADPH regeneration. This bioreduction reaction could be applied to a broad range of prochiral fluoroketones including aryl difluoroketones, aliphatic difluoroketones, and trifluoroacetophenones with excellent conversion and favorable enantioselectivity at high substrate concentrations (100 g L−1). These results indicate the potential of K234 for the industrial production of valuable chiral fluorohydrins. Moreover, this biocatalytic protocol could also be effective without the addition of an external nicotinamide cofactor, which provides useful guidance for further application of ketoreductase K234 in the asymmetric synthesis of chiral secondary alcohols.

Graphical abstract: Biocatalytic asymmetric reduction of fluoroalkyl ketones to access enantiopure fluoroalkyl secondary alcohols

Supplementary files

Article information

Article type
Paper
Submitted
08 Febr. 2023
Accepted
04 Apr. 2023
First published
06 Apr. 2023

Org. Biomol. Chem., 2023,21, 3623-3627

Biocatalytic asymmetric reduction of fluoroalkyl ketones to access enantiopure fluoroalkyl secondary alcohols

Y. Wu, K. Wang, X. Wang, J. Wu and F. Wu, Org. Biomol. Chem., 2023, 21, 3623 DOI: 10.1039/D3OB00193H

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